Synthesis of some 4‐substituted‐2‐(o‐halogenophenyl)‐1,2,3‐triazoles
Document Type
Article
Publication Date
1-1-1983
Department
Department of Chemistry; Department of Chemical Engineering
Abstract
Mesoaldehyde 1,3‐dioxime was treated with either 2,4,6‐trichlorophenyl‐ (a), o‐fluorophenyl‐ (b), or o‐bromophenyl‐ (c) hydrazine to give the corresponding mesoaldehyde 1,3‐dioxime‐2‐halogenophenylhydrazones (1a,b,c). The latter were O‐acetylated with acetic anhydride, and cyclized to triazole 4‐oximes (3b, c) or triazole 4‐O‐acetyloximes (6a,b,c) with cesium carbonate, then converted to nitriles (7a,b,c) by refluxing with acetic anhydride followed by pyrolysis, or to aldehydes (4a,b,c) by hydrolysis. The nitriles (7a,b,c) were also converted to acids (9a,b,c), esters (10a,b,c), amides (8a,c), an alcohol (11a), and an amine (12a). In addition, tetrazoles of two types were prepared. The first (13d,e) were obtained from the acid chlorides by the action of 5‐aminotetrazole, whereas the second (14f) was produced from the respective nitrile by the action of ammonium azide.
Publication Title
Journal of Heterocyclic Chemistry
Recommended Citation
Swartz, D.,
Karash, A.,
Berry, L.,
&
Jaeger, D.
(1983).
Synthesis of some 4‐substituted‐2‐(o‐halogenophenyl)‐1,2,3‐triazoles.
Journal of Heterocyclic Chemistry,
20(6), 1561-1564.
http://doi.org/10.1002/jhet.5570200625
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/3745
Publisher's Statement
Copyright © 1983 Journal of Heterocyclic Chemistry. Publisher’s version of record: https://doi.org/10.1002/jhet.5570200625